Description: Tori Avano is an Army Private who is going to get the anal hazing of a lifetime. Dee Williams and Syren De Mer are two MILF commanders who are going to dish out the punishment with glorious tag-teaming action. Poor young Tori is tied up in bondage with her ass exposed and up in the air, ready to take a spanking. Syren De Mer starts the spanking. She warms up Tori's ass with spankings that turn her tushy hot and pink. Dee Williams finishes the spankings, making Tori's pink cheeks so sensitive that she jumps anytime her ass is touched. Syren grabs her flogger and goes to town on Tori's ass, back, and feet. To start, Tori's asshole gets opened up with a metal toy. These anal punishing MILFs know exactly how to open an asshole properly by giving it a good warm-up. The chemistry between all three of these anal whores is strong. Tori's asshole opens from the sexual energy, and just at the right time to attempt to take Dee William's entire fist. This is Tori Avano's very first ever anal fisting. She really wants to impress her commanders. She attempts to take the fist at first but the feelings are too intense for her. She calls mercy but then begs her commanders to try again. One the second attempt, Dee's entire fist goes in and with her ass full, Tori smashes a vibrator against her own clit and makes herself cum. Veteran ass stretcher, Syren De Mer volunteers to show Tori Avano just how its done. Syren takes a full blown anal punching from Dee Williams. Dee and Syren lick up all the gaping holes they create. Finally, Tori is released from bondage and is fully compliant to taking a good hard lesbian anal strap-on fucking from Dee Williams while Syren holds Tori's gaping asshole open and licks all the freshly fucked flesh.

Description: Mega slut Lily Lane is attending one of the hottest events of the summer -- Lea Lexis' pool party. Lily knows party goers aren't allowed to enter the main house, but after spying her favorite wine through an open window, she can't resist! She sneaks in and starts rummaging through the bar. When Lea catches Lily inside, she knows this slut is after more than just a bathroom. Lea leads Lily to her bedroom, throws her on the bed, and decides to have some fun. She ties Lily up and tugs down her bikini bottoms only to find that Lily is wearing a sparkling jeweled butt plug. Lily is embarrassed and promises to leave immediately if Lea releases her, but Lea isn't about to let that happen, not after finding such a hot slut like Lily Lane stretched open and ready for more. She takes out Lily's buttplug and starts fucking Lily's asshole with big metal dildos. Lily moans as the cold metal dicks stretch out her poor asshole. Lea pops them in and out just to watch Lily's asshole gape over and over again. Next she uses a 2 foot long toy to fill Lily all the way up. Lily is horrified to see what Lea wants to put in her, but her hungry hole swallows up that toy over half way before Lea decides this horny slut ass is ready for her fist. She squeezes all her fingers into Lily and slowly sinks her fist in. Lily cries out as her asshole stretches to accommodate Lea's fist. Seeing Lily's ass all stretched open makes Lea want her ass stretched too. She has Lily insert multiple plugs in her own ass, and once she's got a good gape, she holds her asshole open for Lily to lick. Lily eagerly licks Lea's ass, turning into quite the obedient little whore. Finally Lea breaks out her huge strap-on cock to fuck Lily. Lily moans as Lea pushes her fat cock into her asshole. Lea loves hearing all of Lily's slut noises and fucks Lily nice and deep, ramming her cock all the way into Lily's asshole. Lily loves getting fucked and cums hard all over Lea's cock. Now that Lily's ass is all used up, Lea kicks her out and sends her back outside with her ass all loose and wrecked.

Description: Ariel X brings suspect Maya Kendrick back to the last scene of her crime. Wide eyed Maya claims she's never been here before, but Ariel knows better than to trust the words of this slut. Arial decides to re-enact the events from that night when the criminal known as the Infamous Butthole Fister fisted their last victim. Ariel spanks and sniffs Maya's asshole before sliding a butt plug straight in Maya's ass. Every time Ariel pops it in and out Maya hungry hole gapes wide open ready for more. Ariel pries Maya's asshole open with her fingers to get a good look at Maya's pink insides. Then Ariel grabs the 2 foot long slink monster and pushes it almost all the way in Maya's ass. Maya moans as the toy sinks in, inch by inch, stretching her open and filling up her insides. Now that Maya's hole is properly stretched, Ariel takes turns pushing her fists into Maya's ass. Maya has never been fisted anally before and she loves feeling her asshole swallow Ariel's hands. She cums hard on Ariel's fists over and over again, her body shaking with orgasms. Once that Maya's ass is gaping open, Ariel wants to see what Maya can do to her asshole. Maya slides a fat plug into Ariel's ass and then replaces it with her fist. Ariel can't stop cumming as Maya fist fucks her. With her hand in Ariel, Maya admits she is the culprit! With this confession, Ariel knows she must punish Maya, and fucks her ass with a huge strap-on cock. Maya's eyes flutter up as Ariel pounds her pretty pink asshole. Maya's ass is left raw and gaping -- the fister has become the fisted.

Description: Charlotte Sartre is a very disobedient inmate at the all women's prison. She's been keistering anal toys and copulating with the other female prisoners. The Butthole Prison has brought attention to the Warden on this issue. Anal Warden, Dee Williams is a no nonsense busty MILF who has been known for doing extraordinarily cruel and unusual things to her female inmates. Charlotte denies she's done anything wrong and seems to think she can prove her innocence by NOT being able to fit any toys into her aˆ?tight assaˆ?. If the anal toys don't fit, you must acquit. Unfortunately for anal hungry Charlotte, try as hard as she can to keep her asshole tight, it just wants to stay open and suck up everything in its path. You could drive a truck through Charlotte's loose butthole. Dee starts with a nice firm over the knee spanking. Charlotte's tushy turns bright red and she writhes with pain and pleasure. The spanking isn't enough punishment, so Dee starts fingering and plugging Charlotte's asshole with toys. Charlotte's ass starts gaping wide open and Dee knows right away that she has caught her Anal Toy Smuggler and needs to administer a full anal examination. Dee then has to check the entire asshole so she performs a body cavity search putting her entire fist into Charlotte's ass. Determined to understand how Charlottes has been getting all these toys past the prison inspections, Dee has Charlotte demonstrate how she was able to stretch her ass out for keistering. Charlotte puts a giant red butt plug in Dee's asshole so that Dee can see how easy it is to hide things in buttholes. After learning how Charlotte is doing her bad deeds, Dee must perform one last punishment, She straps on a huge anal dildo and strap on fucks her poor, powerless inmate, leaving her asshole gaping wide open.